The Virgin’s Guide to Great Sex

Surprise! A virgin can actually be better prepared for great sex than many of his or her more precocious peers.

There’s a lot of anxiety surrounding being a virgin. We live in a society that has a notable double-standard on sexuality, especially where virginity is concerned; male virgins (past a certain age) are seen as being immature, incomplete man-children, utter losers who can’t get a woman1. A woman who is a virgin is a vision of innocence and purity… at least until she gets past her early twenties, at which point she’s clearly repressed or otherwise has something wrong with her. Small wonder that being a virgin can be such a source of angst to men and women. One of the issues that I have seen come up over and over again whenever someone mentions being a virgin is the idea that being a virgin is inherently a mark against you; that, by being a virgin at the advanced age of 20, 30, 40, whatever , that not only is there something that makes you undesirable (some ill-defined je ne se quois that apparently others can sense, the way dogs and bees sense fear) but that revealing you’re a virgin will ensure that you will be passed up by others because you lack the experience to provide the mind-blowing sex that we all expect from relative strangers.

Except… being a virgin doesn’t necessarily equal bad sex. In fact, with a little preparation, a virgin can actually be better prepared for sex than many of his or her more precocious peers. Surprise!

50 Shades of Virginity

There are many varying definitions of virginity. When we call someone a virgin, we automatically picture someone who has had next to no sexual experience at all. And yet one can be a virgin who has had considerably more sexual activity than their contemporaries. In modern western society, “sex” almost always equates to “penetrative sex”. The idea that nothing counts besides a penis going into a vagina has led to a brilliant bit of rules-lawyering by teens who want to get around pesky “virginity pledges” or religious restrictions against pre-marital sex by referring to “technical” virginity. Thus, to many, it is possible to be a virgin who has had oral and anal sex, who’s given (or received) hand-jobs and tit-jobs or engaged in mutual masturbation, rolled around naked with hordes of others and has had more sexual experience than their fellows. It only “counts” when the penis has managed to ejaculate into a vagina. One can thus be a virgin and yet give the most amazing head a person could ever receive.

Side note: This, by the way, is a very heteronormative definition of virginity; anal sex evidently does not “count” for women… but apparently does for gay men. And yet many gay men don’t have anal sex. So by this definition, there’re a lot of gay virgins running around out there…

But the majority of virgins who feel this existential dread over their lack of experience tend to be the mostinexperienced; the ones who have had next to no sexual contact whatsoever, whether it be kissing, playing with another person’s junk, dry-humping or even having someone acknowledge one’s erection without pointing and laughter. What hope is there for them? More than you’d think, as it turns out.

Understanding What Makes Great Sex

The first step to great sex—whether you’ve had hundreds of partners or no partners—is to understand that there’s more to sex than Tab A into Slot B, Repeat As Needed. This is one of the aspects that trips up many virgins. They assume that because they haven’t had the all-important First Time that they’re going to be crap in bed… never stopping to think that having had sex once isn’t going to magically make you into a black-belt Fuck-Fu master and Kama Sutra scholar.

Just because someone has had sex before doesn’t mean that they’re going to be a great lay. In fact, a person can have slept with dozens, even hundreds of women and still be worse in bed than someone dealing with a case of involuntary celibacy. Sex, you see, is about more than how many tricks and secret techniques you’ve learned. It’s not just about being able to give the Transylvanian Twist or the Swirly-Go-Round. In fact, some “killer” sex techniques (especially any recommended by Cosmo) will more likely get you thrown out of bed instead of being hailed as a godly lover.

Good sex isn’t just about nifty tricks involving mashing your genitals together, it’s about your mindset. It isn’t about having a big cock – in fact, that tends to make men worse lovers. It’s not about having long legs, or a tight ass or dick-sucking lips. It’s not about what’s going on between your legs, it’s about what’s going on between your ears. The biggest key to good sex isn’t experience so much as attitude. A person with a can-do attitude, an ability to listen and a willingness to take direction without complaint or letting their ego get in the way makes a far better lover than someone who’s plowed his way through dozens of drunken hookups with nary a thought beyond getting his dick wet. Yes, it may be a little awkward at first… except every first sexual encounter tends to be awkward; you’re dealing with a relative stranger, with his or her own preferences, turn-ons and deal-breakers. There are no universal secrets to pleasing another person, man or woman. Not every guy loves blowjobs. Not every woman likes cunnilingus. One person’s patented oral technique may deliver screaming orgasms with one partner and set another’s skin to crawling. Some may like a finger up the backdoor while others may react violently. Yes, experience is the great teacher… but only if you’re getting the right lessons in the first place. I’ve lost track of how many people I’ve known who thought they were God’s own cocksmen, but whose girlfriends would later confide that they faked their orgasms. As a result: you have men going around convinced that they possess divine sex powers… right up until they encounter the first woman who didn’t have a problem letting him know exactly how shit he was in bed. Being willing to learn and being able to handle criticism withoutfreaking out, falling apart or getting argumentative is a much bigger component of sexual satisfaction. Being a giving lover with a genuine interest in your partner’s pleasure – making sex about the two of you rather than a case of “easy cum, easy go” – will reward you far more than just mindlessly banging anyone who happens to say “yes” once. Speaking of learning the right lessons…

Touch Yourself (to Know Yourself)

Now, odds are that if you’re a virgin and don’t want to be, you’ve had some marathon masturbation sessions in your time. All well and good; sometimes all a person wants is a quick “wham, bam, thank you glans”. However, if you’ve been mindlessly jerking it, you’re missing out on a critical part of great sex. Sure, you know how to make yourself cum… you can do it with your eyes closed and one hand tied behind your back and your parents pounding on the bathroom door demanding to know what the hell you’re doing in there. But do you know how to tell someone else how to give you mind-blowing orgasms? Think about it for a second. How many times have you stopped and really analyzed what it is you’re doing when you’re indulging in some quality alone time? What we do to get ourselves off is an important part of sex… because it’s information our partners would rather dearly like to know. We like to make jokes-that-aren’t-really-jokes about how guys are easy to please and every guy jerks it the exact same way… but it’s not really true.

Just as no two women masturbate the same way, neither do guys. Some guys need more stimulation to the underside of the glans while others need pressure more than friction. Some need more varied friction while others do better with a specific rhythm. This is all valuable information to know… after all, how’s a partner supposed to get you off when you don’t know what you need? It’s also possible for guys to actually make itharder ((Phrasing!)) for others to get them off; many guys actually desensitize themselves by using an extreme level of pressure or friction that the human body just can’t match; they jerk themselves through their clothing, or rub themselves against a wash cloth or a carpet. They may use what Dan Savage has termed “the death grip” where they squeeze their penis like it owes them money; some guys masturbate by humping their mattress or the space between the bed and box-spring. As a result: they can’t orgasm through regular sexual contact – much to their (and their partner’s) frustration. This is one reason why I advise guys to invest in a masturbation sleeve like a Fleshlight or a Tenga—it’s a great way to ensure that you don’t train yourself to learn the wrong lessons (as it were) from solo sex. They’re also much closer to the feel of sex with another person—helping familiarize yourself with your own orgasm response during penetrative sex… not to mention helping build up some endurance so that you don’t fear being a two-pump chump.

Similarly, women benefit from familiarity with themselves. One of the most common complaints that couples have during sex is the feeling that they should be having Look-Ma-No-Hands orgasms. The problem is, only a small minority of women are able to orgasm strictly from penetration; the vast majority require some form of clitoral stimulation… and even then, the level and type of stimulation will vary from woman to woman. Simply put, many women will need a helping hand… or handy device for that matter. Some women require very intense, direct clitoral stimulation—sometimes a level of intensity that only a vibrator can give—while others are easier to get off than a pair of shoes. The better you know yourself—whether you need direct contact with the clit or slightly off to the sides, whether you’re very sensitive and require the lightest of touches or you need someone to bury their face right on top—the better able you are to guide your partner.

Be sure to vary your masturbation routines—using more lube, less lube, switching hands, or different types of stim in order to keep from developing a specific habit that might keep you from being able to achieve any sort of climax with a partner. And guys: start using condoms as part of your masturbation routine. Not only will it make for easier clean-up, but it will familiarize you with finding condoms that are the right size2 and how to put them on correctly and efficiently with minimal fuss or fumbling… not to mention teaching you that no they don’t desensitize you or make it impossible to feel anything. For extra sensation, use a small amount of a water-based lubricant on the inside of the condom; squirt it into the tip before rolling it on. You’ll be amazed at the difference that it makes to the experience… whether by yourself or with a partner.

Just remember: until you’re in a mutually monogamous relationship of long-standing and you’ve both been tested for STI’s, condoms are mandatory.

Use Your Words

If you’ve been reading the blog for a while you may have noticed just how often “communication” comes up. There’s a good reason for this. Communication is one of the most vital skills when it comes to any sort of relationship, whether it’s one that’s lasted for years or for thirty minutes of grunting and squishy noises. Being able to communicate with your partner is key to good sex, regardless of how much experience you have or haven’t had. Good sex is about both parties working together and that requires being able to actually talk to them, to understand them and be understood. It’s not just a matter of being able to say “No, more pressure here” or “Less teeth”, it’s about being able to be up front if you’re having last minute doubts or feeling anxious about some issue or another. It’s about being able to talk about contraceptives, about consent, about limits, what you may or may not be up for or willing to try. It’s about being able to be honest with the person you’re sleeping with, including the fact that you’re a virgin. Some people may be hesitant to have sex with a virgin, not because they’re afraid of bad sex but because they may worry about what it means. It’s a popular myth/fear that a woman3 will fixate on the person she loses her virginity to like a baby gosling looking for its mommy. Not everybody is going to lose their virginity over the course of a romantic relationship. Just as many – men and women – are likely to find a willing partner for some no-strings attached sex. Quite frankly, if you can’t have an honest and frank conversation about sex with someone, you probably shouldn’t be sleeping with them in the first place.

Don’t Buy The Hype

One thing to keep in mind: there are a lot of popular – if inaccurate – ideas that still float around about the first time that are often a source of anxiety. Some examples:

A male virgin is going to be a one-minute wonder

Some men will be, yes… but then again, this is also true regardless of whether they’re virgins or not. Some folks are a little quicker on the trigger than others. Many men however, find that they actually have a hard time reachingorgasm at all; the self-inflicted pressure to perform and the sudden new and strange sensations are so much that it actually makes it difficult to come. As a result: things actually become painful for their partner. There is such a thing as too much hang-time. In these cases, it’s better to stop and let things calm down for a while – possibly switching to oral sex or masturbation instead.

A woman’s first time is going to suck/be painful and/or awkward

Again: sometimes yes. Just as often: not really. It can be awkward, even uncomfortable – after all, it’s a new and completely unfamiliar sensation. Even masturbation isn’t necessarily going to prepare you for the sensations of actually having sex. At times when it is painful, it’s usually quick and manageable and can be eased by plenty of lube and going slowly and gently, not letting the guy pound away like a jackhammer.

She has to have an orgasm for the sex to be great

A lot of guys have an issue with orgasms: they’re obsessed with whether the women they’re with had them. While on the surface this can be a good thing – after all, you want a partner who’s as concerned with your pleasure as they are with their own – it can also lead to increased pressure on the woman… which in turn can inhibit orgasms. Men tend to be orgasm-focused because it’s a lot easier for men to have them. As a result, we tend to see orgasms as the end-all, be-all of sex. If we don’t have one, something’s clearly not right, therefore if she doesn’t have one… Thing is though: women can and do enjoy sex even if they don’t necessarily get off… and not every woman can get off during actual intercourse. Sometimes it’s just not going to happen, especially if it’s your first time. And that’s OK.

Sex ends when he comes

Speaking of: guys tend to treat their orgasm as the closing ceremonies. It’s a cliche as old as time: he gets off, rolls over and starts to snore, leaving his partner frustrated and annoyed. Yes, guys tend to lose interest when they blow their loads and a male’s refractory time is longer than a woman’s… but just because you came doesn’t mean that things come to a screeching halt. You may have gotten your rocks off, but that doesn’t mean that your partner wouldn’t want more head or a manual assist or two… especially if you’re worried about not lasting long enough.

Sex changes everything

The biggest problem that people face with their first time is that they build it up in their heads to an all-encompassing, cataclysmic event that will revolutionize their entire world. As a result: sex becomes this massive, mythic thing of critical importance, desirable and bowel-quakingly intimidating at the same time. Real talk: you will be exactly the same person after your first time as you were before. The difference between being a virgin and not is a matter of a new set of experiences. You won’t be any more attractive or adult for having finally had an orgasm with an assist from another person. Having the intimate knowledge of what the inside of a vagina feels like isn’t going to magically take away your insecurities or transform you into someone new. People aren’t going to be looking at you thinking “They had sex last night,” with knowing smirks of newfound respect. The more you build up losing your virginity in your head, the harder of a time you’re going to have making it happen at all. By equating sex with being the alpha and omega of your self-worth, you’re actually making it harder on yourself by holding yourself to unreachable (and unfair) standards. You need to relax. Take a deep breath. Sex, after all, is supposed to be fun. It’s supposed to be enjoyable. And with a little preparation and the right mindset… your first time can be amazing.

Harris O'Malley provides geek dating advice at his blog Paging Dr. NerdLove, as well as writing the occasional guest review for Spill.com and appearing on the podcast The League of Extremely Ordinary Gentlemen. He can be found dispensing snark and advice on Facebook and Twitter (@DrNerdLove.)

I thinkis is also a myth that women necessarily want P in V intercourse to last for a long time. It’s true that women often need 15 or more minutes of clitoral stimulation to reach orgasm but at the same time, more than 15 minutes of penetration starts to get tiring (at least for me personally). More than 30 minutes and it definitely may get painful. My boyfriend usually makes sure that I have an orgasm first (through manual or oral stimulation – he’s such a fine gentleman!) and after that, I’m not to concerned about how long he “lasts.”

I agree! I’m lucky that it doesn’t get painful, but I do sometimes get bored, which in itself is tiring. I don’t think of this as a problem either, so I’m not interested in how I can fix it. It’s just how it is, and once I get that “yeeeep, that’s enough, not interested any more” feeling then I don’t mind waiting for my partner to finish up. Sometimes I can go ages and still be enjoying it, other days I’m 10 minutes in and thinking “Just get on with it already!” Especially if my mental “To Do” list is overflowing. A lot of the time the non-penetrative stuff is more fun anyway and promotes a lot more communication. Guys shouldn’t worry so much about having to “last” for us ladies, just worry about whether we’re enjoying it as much as you are!

Problem I had was pills blocked orgasms, I would get to that point just before orgasm where you feel all ze fluids getting ready, you’d feel the blood flow increase bigtime, then nothing. So SO frustrating, my first experience of sex was like that and it was over an hour or more before I did orgasm. It made sex utterly frustrating and not enjoyable because it results in a lot of pain (“blueballs”) and personally the frustration was quite large.

Once I got off them I could orgasm a lot faster, sometimes mere minutes, but I do last a while. I also learned where the points are in the pleasure to avoid orgasmif I need to extend it out for some reason.

“My boyfriend usually makes sure that I have an orgasm first (through manual or oral stimulation – he’s such a fine gentleman!) and after that, I’m not to concerned about how long he “lasts.””
Sounds great. I will definitely try that. Knowing that PIV doesn’t give all women an orgasm was very important to learn so I am definitely aware of that now.

Is it just me, or doesn’t it always seem to be par for the course that the people who have (had) and/or can enjoy sex with a partner pretty much whenever they like, always seem to find it of less important than the people who can’t or haven’t…?

I ror one think that this speaks more for the value of the human psyche of “always wanting what we can’t have”, than for the actual importance or value of having sex.

Yes. Sex is supposed to be fun and enjoyable. Why else do you think that people fret about not having it enough? Because they think they won’t like it?

I’ve always likened it to a cute little analogy that is used a lot at love-shy.com. Sex is like food and those who never had it trying to imagine it is like a starving man trying to imagine what it must be like to eat a steak. Whereas people who have already had sex (and get it at least on a semi-regular basis), are like people who always seem to have enough money to eat out at the finest steak house and have eaten so much steak that they don’t see it as such a huge deal anymore.

The countless deaths of unarmed black men by police, coupled with persistent activism from communities of color, has forced the conversation of race on America, causing officials to reevaluate, among many things, how policing is done.